EP0576330B1 - Neues Verfahren zur Herstellung Delta-9(11)-Steroide - Google Patents

Neues Verfahren zur Herstellung Delta-9(11)-Steroide Download PDF

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Publication number
EP0576330B1
EP0576330B1 EP93401555A EP93401555A EP0576330B1 EP 0576330 B1 EP0576330 B1 EP 0576330B1 EP 93401555 A EP93401555 A EP 93401555A EP 93401555 A EP93401555 A EP 93401555A EP 0576330 B1 EP0576330 B1 EP 0576330B1
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EP
European Patent Office
Prior art keywords
compound
temperature
formula
process according
producing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP93401555A
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English (en)
French (fr)
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EP0576330A1 (de
Inventor
Jean Buendia
Patrick Roussel
Michel Vivat
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aventis Pharma SA
Original Assignee
Roussel Uclaf SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Roussel Uclaf SA filed Critical Roussel Uclaf SA
Publication of EP0576330A1 publication Critical patent/EP0576330A1/de
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Publication of EP0576330B1 publication Critical patent/EP0576330B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0094—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 containing nitrile radicals, including thiocyanide radicals

Definitions

  • the present invention relates to a new process for the preparation of a steroid compound ⁇ 9 (11).
  • the subject of the invention is therefore an industrial process for the preparation of the compound of formula (I): from a compound of formula (II): characterized in that the compound of formula is treated with chlorosulfonic acid in an organic solvent.
  • the operation is carried out in a polar aprotic solvent chosen from the group consisting of tetrahydrofuran, dioxane and acetone, or ethyl acetate or methylene chloride, tetrahydrofuran and acetone being very particularly preferred, and the reaction is carried out first at a temperature of -20 ° to -10 ° C, preferably -15 ° C, then allowing to rise the temperature at 0 ° / + 10 ° C, preferably + 5 ° C.
  • a polar aprotic solvent chosen from the group consisting of tetrahydrofuran, dioxane and acetone, or ethyl acetate or methylene chloride, tetrahydrofuran and acetone being very particularly preferred
  • chlorosulfonic acid has already been used as a steroid series dehydrating agent to prepare ⁇ 9 (11) compounds from the corresponding 9 ⁇ -OH compounds (see French patent 2,387,245).
  • the process of the invention derives its selectivity from the conditions under which it is carried out.
  • the sulfonate is first selectively formed at an appropriate temperature, the rise in temperature then being necessary for elimination leading to the formation of the double bond ⁇ 9 (11).

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Toxicology (AREA)
  • General Health & Medical Sciences (AREA)
  • Steroid Compounds (AREA)
  • Saccharide Compounds (AREA)

Claims (5)

  1. Verfahren zur Herstellung einer Verbindung der Formel (I)
    Figure imgb0007
     ausgehend von einer Verbindung der Formel (II)
    Figure imgb0008
     dadurch gekennzeichnet, daß man die Verbindung der Formel (II) in einem organischen Lösungsmittel mit Chlorsulfonsäure behandelt.
  2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, daß man in einem polaren aprotischen Lösungsmittel arbeitet, gewählt aus der durch Tetrahydrofuran, Dioxan und Aceton, oder Ethylacetat oder Methylenchlorid gebildeten Gruppe.
  3. Verfahren nach Anspruch 2, dadurch gekennzeichnet, daß man in Tetrahydrofuran oder Aceton arbeitet.
  4. Verfahren nach irgendeinem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß man bei einer Temperatur von -20 °C bis -10 °C arbeitet und anschließend wieder auf eine Temperatur von 0 °C/+5 °C ansteigen läßt.
  5. Verfahren nach Anspruch 4, dadurch gekennzeichnet, daß man bei einer Temperatur von -15 °C arbeitet und anschließend wieder auf eine Temperatur von +5 °C ansteigen läßt.
EP93401555A 1992-06-19 1993-06-17 Neues Verfahren zur Herstellung Delta-9(11)-Steroide Expired - Lifetime EP0576330B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9207460A FR2692580B1 (fr) 1992-06-19 1992-06-19 Nouveau Procédé de préparation d'un composé stéroïde DELTA9 (11).
FR9207460 1992-06-19

Publications (2)

Publication Number Publication Date
EP0576330A1 EP0576330A1 (de) 1993-12-29
EP0576330B1 true EP0576330B1 (de) 1995-09-27

Family

ID=9430926

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93401555A Expired - Lifetime EP0576330B1 (de) 1992-06-19 1993-06-17 Neues Verfahren zur Herstellung Delta-9(11)-Steroide

Country Status (10)

Country Link
US (1) US5399727A (de)
EP (1) EP0576330B1 (de)
JP (1) JP3340514B2 (de)
AT (1) ATE128471T1 (de)
CA (1) CA2098804C (de)
DE (1) DE69300546T2 (de)
DK (1) DK0576330T3 (de)
ES (1) ES2077475T3 (de)
FR (1) FR2692580B1 (de)
HU (1) HU213607B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5641765A (en) * 1992-11-18 1997-06-24 Smithkline Beecham Corporation 17-αand 17-βsubstituted acyl-3-carboxy-3,5-dienes and use in inhibiting 5-α-reductase
HU224216B1 (hu) 2000-06-05 2005-06-28 Csapláros László Hidroxi-benzoesav származékok, eljárás előállításukra és ezeket tartalmazó antiplazmid hatású gyógyszerkészítmények
EP4134373A1 (de) 2021-08-12 2023-02-15 Santhera Pharmaceuticals (Schweiz) AG Synthese von delta-9,11-steroiden

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4127596A (en) * 1977-04-11 1978-11-28 The Upjohn Company Non-aromatic oxygenated strong acid dehydration of 9α-hydroxyandrostenediones
US5352809A (en) * 1986-10-10 1994-10-04 Gist-Brocades N.V. 9-alpha-hydroxy steroids, process for their preparation, process for the preparation of the corresponding 9(11)-dehydro derivatives and pharmaceutical preparations containing such steroids
PT87687B (pt) * 1987-06-12 1992-09-30 Gist Brocades Nv Processo para a preparacao de esteroides de 9(11)-dehidro

Also Published As

Publication number Publication date
DK0576330T3 (da) 1996-02-12
JP3340514B2 (ja) 2002-11-05
EP0576330A1 (de) 1993-12-29
HU213607B (en) 1997-08-28
US5399727A (en) 1995-03-21
FR2692580B1 (fr) 1994-08-26
CA2098804C (fr) 2003-07-29
HU9301790D0 (en) 1993-09-28
DE69300546D1 (de) 1995-11-02
JPH0656882A (ja) 1994-03-01
DE69300546T2 (de) 1996-04-11
FR2692580A1 (fr) 1993-12-24
ATE128471T1 (de) 1995-10-15
CA2098804A1 (fr) 1993-12-20
ES2077475T3 (es) 1995-11-16
HUT64559A (en) 1994-01-28

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